US3429907A - Amine cyanoferrates and methods for preparing same - Google Patents
Amine cyanoferrates and methods for preparing same Download PDFInfo
- Publication number
- US3429907A US3429907A US504181A US3429907DA US3429907A US 3429907 A US3429907 A US 3429907A US 504181 A US504181 A US 504181A US 3429907D A US3429907D A US 3429907DA US 3429907 A US3429907 A US 3429907A
- Authority
- US
- United States
- Prior art keywords
- ferrocyanide
- grams
- mole
- water
- milliliters
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001412 amines Chemical class 0.000 title description 13
- 238000000034 method Methods 0.000 title description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 32
- -1 amine salt Chemical class 0.000 description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 239000002244 precipitate Substances 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- 238000004458 analytical method Methods 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 241000195493 Cryptophyta Species 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YAGKRVSRTSUGEY-UHFFFAOYSA-N ferricyanide Chemical compound [Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] YAGKRVSRTSUGEY-UHFFFAOYSA-N 0.000 description 8
- JFSUDVTVQZUDOP-UHFFFAOYSA-N tetrasodium;iron(2+);hexacyanide;decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[Na+].[Na+].[Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] JFSUDVTVQZUDOP-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- VRWKTAYJTKRVCU-UHFFFAOYSA-N iron(6+);hexacyanide Chemical compound [Fe+6].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] VRWKTAYJTKRVCU-UHFFFAOYSA-N 0.000 description 7
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- AJJBNKUPXKYSKX-UHFFFAOYSA-N 3-dodecylsulfanylpropan-1-amine Chemical compound CCCCCCCCCCCCSCCCN AJJBNKUPXKYSKX-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 5
- YAGKRVSRTSUGEY-UHFFFAOYSA-Q hydron;iron(3+);hexacyanide Chemical compound [H+].[H+].[H+].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] YAGKRVSRTSUGEY-UHFFFAOYSA-Q 0.000 description 5
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 5
- TWXCJZHSMRBNGO-UHFFFAOYSA-N 3-decoxypropan-1-amine Chemical compound CCCCCCCCCCOCCCN TWXCJZHSMRBNGO-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 4
- PLZVEHJLHYMBBY-UHFFFAOYSA-N Tetradecylamine Chemical compound CCCCCCCCCCCCCCN PLZVEHJLHYMBBY-UHFFFAOYSA-N 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- RDCAZFAKCIEASQ-UHFFFAOYSA-N 3-octoxypropan-1-amine Chemical compound CCCCCCCCOCCCN RDCAZFAKCIEASQ-UHFFFAOYSA-N 0.000 description 3
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 3
- 150000003973 alkyl amines Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 2
- DFAIOPNYWLGZTO-UHFFFAOYSA-N 3-[2-(2-ethoxyethoxy)ethoxy]propan-1-amine Chemical compound CCOCCOCCOCCCN DFAIOPNYWLGZTO-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 159000000021 acetate salts Chemical class 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002353 algacidal effect Effects 0.000 description 2
- 239000003619 algicide Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- FKOPCVJGLLMUNP-UHFFFAOYSA-N decylazanium;acetate Chemical compound CC(O)=O.CCCCCCCCCCN FKOPCVJGLLMUNP-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052717 sulfur Chemical group 0.000 description 2
- 239000011593 sulfur Chemical group 0.000 description 2
- YKWGACFVMGKCLG-UHFFFAOYSA-N 2-ethyldecan-1-amine Chemical compound CCCCCCCCC(CC)CN YKWGACFVMGKCLG-UHFFFAOYSA-N 0.000 description 1
- HFYBEMAOWNXNDL-UHFFFAOYSA-N 3-dodecylsulfanylpropanenitrile Chemical compound CCCCCCCCCCCCSCCC#N HFYBEMAOWNXNDL-UHFFFAOYSA-N 0.000 description 1
- BZXNODUHVHSEIA-UHFFFAOYSA-N 3-octylsulfanylpropan-1-amine Chemical compound CCCCCCCCSCCCN BZXNODUHVHSEIA-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 241000195628 Chlorophyta Species 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 241000192700 Cyanobacteria Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910052729 chemical element Inorganic materials 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- HBRNMIYLJIXXEE-UHFFFAOYSA-N dodecylazanium;acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN HBRNMIYLJIXXEE-UHFFFAOYSA-N 0.000 description 1
- XXUJMEYKYHETBZ-UHFFFAOYSA-N ethyl 4-nitrophenyl ethylphosphonate Chemical compound CCOP(=O)(CC)OC1=CC=C([N+]([O-])=O)C=C1 XXUJMEYKYHETBZ-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- UPHWVVKYDQHTCF-UHFFFAOYSA-N octadecylazanium;acetate Chemical compound CC(O)=O.CCCCCCCCCCCCCCCCCCN UPHWVVKYDQHTCF-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000000276 potassium ferrocyanide Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- GTSHREYGKSITGK-UHFFFAOYSA-N sodium ferrocyanide Chemical compound [Na+].[Na+].[Na+].[Na+].[Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] GTSHREYGKSITGK-UHFFFAOYSA-N 0.000 description 1
- 239000000264 sodium ferrocyanide Substances 0.000 description 1
- 235000012247 sodium ferrocyanide Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- ZXQVPEBHZMCRMC-UHFFFAOYSA-R tetraazanium;iron(2+);hexacyanide Chemical compound [NH4+].[NH4+].[NH4+].[NH4+].[Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] ZXQVPEBHZMCRMC-UHFFFAOYSA-R 0.000 description 1
- XOGGUFAVLNCTRS-UHFFFAOYSA-N tetrapotassium;iron(2+);hexacyanide Chemical compound [K+].[K+].[K+].[K+].[Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] XOGGUFAVLNCTRS-UHFFFAOYSA-N 0.000 description 1
- UTYXJYFJPBYDKY-UHFFFAOYSA-N tetrapotassium;iron(2+);hexacyanide;trihydrate Chemical compound O.O.O.[K+].[K+].[K+].[K+].[Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] UTYXJYFJPBYDKY-UHFFFAOYSA-N 0.000 description 1
- DCXPBOFGQPCWJY-UHFFFAOYSA-N trisodium;iron(3+);hexacyanide Chemical compound [Na+].[Na+].[Na+].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] DCXPBOFGQPCWJY-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/25—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/04—Nitrogen directly attached to aliphatic or cycloaliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
- C10M159/18—Complexes with metals
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/08—Inorganic acids or salts thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/08—Inorganic acids or salts thereof
- C10M2201/081—Inorganic acids or salts thereof containing halogen
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/08—Inorganic acids or salts thereof
- C10M2201/082—Inorganic acids or salts thereof containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/08—Inorganic acids or salts thereof
- C10M2201/084—Inorganic acids or salts thereof containing sulfur, selenium or tellurium
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
- C10M2215/26—Amines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2221/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2221/043—Polyoxyalkylene ethers with a thioether group
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/14—Group 7
Definitions
- R is an acyclic alkyl radical
- R is an acyclic alkyl radical or an acyclic alkoxyalkoxyalkyl radical
- R" is an acyclic alkylene bridge
- X is oxygen or sulfur
- m is an integer from 3 to 4.
- the compounds have particular utility as algicides.
- the present invention relates to novel amine cyanoferrates and to methods for preparing the same. More particularly, it relates to novel amine cyanoferrates of the formula:
- R is an alkyl substituent containing from 6 to 18 carbon atoms; R represents an alkyl substituent containing from 4 to 14 carbon atoms or an alkoxyalkoxyalkyl substituent containing from 6 to 16 carbon atoms; X is either oxygen or sulfur; R" is an alkylene bridge containing from 2 to 4 carbon atoms; and m represents the integer 3 or 4.
- each of the novel amine cyanoferrates hereinabove defined find utility as antioxidants, lube oil additives and possess nematocidal and algicidal activity as Well.
- each of the novel amine cyanoferrates can be prepared by reacting an appropriate amine with either a ferricyanic acid or ferrocyanic acid.
- the compounds of the present invention can be readily prepared by reacting (I) an appropriate amine, such as (a) an alkyl amine as for instance, hexylamine, octylamine, dodecylamine or octadecylamine, (b) an alkyloxyalkylamine, such as 3-decyloxypropylamine, (c) an alkylthioalkylamine, such as 3-(dodecylthio)propylamine or (d) an alk0xyalkoxyalkoxyalkylamine, such as 3-(ethoxyethoxyethoxy)ethylamine or 3-(methoxypropoxypropoxy)ethylamine with (II) either ferrocyanic acid or ferricyanic acid.
- an appropriate amine such as (a) an alkyl amine as for instance, hexylamine, octylamine, dodecylamine or octadecylamine
- ferrocyanic acid approximately 4 mole proportions of the appropriate amine are reacted with 1 mole proportion of the corresponding acid.
- ferricyanic acid approximately 3 mole proportions of the appropriate amine are reacted with 1 mole proportion of the ferricyanic acid.
- the reaction takes place in an alcoholic medium.
- the latter illustratively includes methanol, ethanol and propanol. Thereafter, the desired product precipitates and is recovered, for instance, by filtration.
- a water soluble amine salt such as the hydrochloride or acetate salt of the appropriate amine
- a water-soluble ferrocyanide or water-soluble ferricyanide such as, for instance, potassium ferrocyanide, sodium ferricyanide or ammonium ferrocyanide.
- a further alternative involves the reaction between an appropriate amine per se and an acidified aqueous solution of an alkali metal salt, such as sodium ferrocyanide or potassium ferricyanide, wherein the latter reactant is formed in situ as an acid.
- an alkali metal salt such as sodium ferrocyanide or potassium ferricyanide
- Decylamine ferricyanide Dodecylamine ferrocyanide, Dodecylamine ferricyanide, Tetradecylamine ferrocyanide, Tetradecylamine ferricyanide, Hexadecylamine ferrocyanide, Hexadecylamine ferricyanide, Octadecylamine ferrocyanide, Octadecylamine ferricyanide, l-methylundecylamine ferrocyanide, l-methylundecylamine ferricyanide, l-methyldodecylamine ferrocyanide, l-methyldodecylamine ferricyanide, l-methyltridecylamine ferrocyanide, l-methyltridecylamine ferricyanide, 2-ethyldecylamine ferrocyanide, Z-ethyldecylamine ferricyanide, 3-butylhexy1amine ferrocyanide, 3-butylhexylamine ferricyanide, 2-
- EXAMPLE 1 Preparation of dodecylamine ferrocyanide A solution of 18.5 grams (0.10 mole) of dodecylamine in water containing a slight excess of hydrochloric acid is diluted to milliliters and added with stirring to a solution of 12.1 grams (0.025 mole) of sodium ferrocyanide decahydrate in 39 milliliters of water. The mixture is diluted to about 400 milliliters with water, and the creamcolored precipitate is cfiltered, washed thoroughly with water, ethanol and ether, respectively, and then dried in vacuo. A yield of 23.4 grams of desired product having an indefinite melting point between 270 C. and 320 C. is obtained.
- EXAMPLE 2 Preparation of tetradecylamine ferrocyanide A solution of 2.16 grams (0.010 mole) of ferrocyanic acid (prepared by precipitation with hydrochloric acid from an aqueous solution of potassium ferrocyanide trihydrate and subsequent filtration) in 100 milliliters of ethanol is added with stirring to a solution of 8.54 grams (0.040 mole) of tetradecylamine in 300 milliliters of ethanol. The solid precipitate is filtered, washed with ethanol, and dried in vacuo. A yield of 8.46 grams of a light green solid whose melting point is indefinite is obtained with color changes above 150 C.
- EXAMPLE 4 Preparation of l-methyldodecylamine ferrocyanide A solution of 6.1 grams (0.013 mole) of sodium ferrocyanide decahydrate in 200 milliliters of water is added gradually with stirring to a solution of 13.0 grams (0.05 mole) of l-methyldodecylamine acetate, prepared from l-methyldodecylamine and acetic acid in ether, in 200 milliliters of water. The resulting precipitate is filtered, washed thoroughly with water, dried, then washed with ether, and redried. The yield of desired product is 11.5 grams and possesses an indefinite melting point, with color changes above about 140 C.
- EXAMPLE 5 Preparation of octylamine ferrocyanide A solution of 2.6 grams (0.02 mole) of octylamine in 200 milliliters of ethanol is added to a solution of 1.1 grams (0.005 mole) of ferrocyanic acid in 150 milliliters of ethanol. The resulting precipitate is filtered, washed with ethanol, and dried in vacuo. Yield 2.0 grams (55% of theory); melting point is indefinite, .with color changes above about 190 C. The product is indicated by analysis to contain molecule of ethanol of crystallization per molecule of ferrocyanide salt.
- EXAMPLE 6 Preparation of decylamine ferricyanide A solution of 4.8 grams (0.015 mole) of potassium ferricyanide in 50 milliliters of Water is added slowly with stirring to a solution of 10.0 grams (0.046 mole) of decylamine acetate in 75 milliliters of water. The resulting sticky yellow precipitate is filtered, washed with water, and redissolved in ethanol. The ethanol solution is filtered and the filtrate is diluted with ether. The reddish waxy precipitate is filtered, and again dissolved in ethanol and precipitated with ether. The final precipitate is filtered and dried. A yield of 3.9 grams of desired product whose melting point is indefinite is obtained.
- EXAMPLE 7 Preparation of dodecylamine ferricyanide A solution of 1.1 grams (0.003 mole) of potassium ferricyanide in 5 milliliters of water is added slowly with stirring to a solution of 2.5 grams (0.01 mole) of dodecylamine acetate in 15 milliliters of water. The resulting yellow precipitate is filtered, washed with water, dissolved in ethanol, and the solution filtered and diluted with ether. The yellow solid is filtered, washed with ether and dried to recover 2.4 grams of desired product having an indefinite melting point with color changes above C.
- EXAMPLE 8 Preparation of hexadecylamine ferrocyanide A solution of 7.2 grams (0.03 mole) of hexadecylamine in milliliters of ethanol is added to a solution of 1.6 grams (0.075 mole) of ferrocyanic acid in 15 milliliters of ethanol. The resulting precipitate is filtered, washed with ethanol, then with ether, and dried in vacuo. A yield of 8.2 grams having an indefinite melting point with color changes above about 150 C. is noted.
- EXAMPLE 10 Preparation of 3-(octyloxy)propylamine ferrocyanide A mixture of 7.5 grams (0.04 mole) of 3-(octyloxy) propylamine and 2.4 grams (0.04 mole) of acetic acid is dissolved in 200 milliliters of warm water. A solution of 4.8 grams (0.01 mole) of sodium ferrocyanide decahydrate in 50 milliliters of water is added with stirring. The resulting precipitate is filtered, washed with water, then with ethanol, and dried in vacuo. It is triturated with methylene chloride and redried. A yield of 7.8 grams of desired product whose melting point is C.-l80 C.
- wtih decomposition is obtained and analyzes in percent as folloWs.Calcd for C H FeO N C, 62.21; H, 10.86; N, 14.51; Fe, 5.79. Found: C, 62.04; 'H, 10.70; N, 14.26; Fe, 6.11.
- EXAMPLE 12 Preparation of octadecylamine ferrocyanide A solution of 6.0 grams (0.018 mole) of octadecylamine acetate in a mixture of 620 milliliters of water, 2 milliliters of acetic acid, and 150 milliliters of ethanol is prepared with gentle warming. A solution of 2.17 grams (0.0045 mole) of sodium ferrocyanide decahydrate in 10 milliliters of water is added gradually with stirring. The mixture is stirred 10 minutes more, and the greenish solid is filtered, washed with water and with methanol and airdried.
- EXAMPLE 13 Preparation of 3-(decyloxy)propylarnine ferrocyanide A mixture of 5.0 grams (0.023 mole) of 3-(decyloxy)- propylamine and 3.0 grams (0.050 mole) of glacial acetic acid in ether is evaporated to dryness. The resultant solid amine acetate is dissolved in 50 milliliters of water, and treated gradually with stirring with a solution of 2.75 grams (0.0057 mole) of sodium ferrocyanide decahydrate in about 20 milliliters of water. The mixture is stirred 5 minutes more and the off-white solid precipitate is filtered oil and washed well with water, then with methylene chloride. It is dried in vacuo.
- Yield of desired product is 4.9 grams and analyzes (in percent) as follows.Calcd for C H N O Fe: C, 64.65; H, 11.23; N, 13.00; Fe, 5.18. Found: C, 64.49; H, 11.26; N, 12.87; Fe, 5.35.
- EXAMPLE 14 Preparation of 3-(dodecylthio)propylamine ferrocyanide A solution of sodium ferrocyanide decahydrate (1.88 grams, 0.0039 mole) in about milliliters of water is added gradually with stirring to a solution of 5.00 grams (0.0156 mole) of 3-(dodecylthio)propylamine acetate in 50 milliliters of water. The mixture is stirred for an additional 10 minutes and the light-colored solid precipitate is filtered off, washed thoroughly with water, then with acetone, and dried. A 3.7 gram yield of desired product whose melting point is indefinite is obtained.
- the 3-(dodecylthio)propylamine is readily prepared from a reduction of 3-(dodecylthio) propionitrile by means of lithium aluminum hydride and followed by conversion to the acetate salt by treatment in ether solution with glacial acetic acid.
- EXAMPLE 17 To demonstrate the algicidal activity of the compounds of the instant invention, samples of mixed cultures of unicellular, multicellular and filamentous green algae obtained from a fish tank and filamentous type blue-green algae isolated from a paper mill settling pond and tentatively designated as black algae are selected for treatment with 1, 5 or 10 p.p.m. of the compounds of the instant invention.
- Appropriate dilutions of test compounds made in Chous media for culture of algae are prepared. Ten milliliter portions of each solution are placed in test tubes and two drops of a stock culture of algae are added to each tube as an inoculum. The inoculated tubes are incubated in a light culture room with about 2000-foot candles light intensity at a temperature of about 78 and a relative humidity of 60%. Incubation is continued for 7 days, then all tubes are examined for algae proliferation.
- alkylamine ferrocyanide containing less than six carbon atoms in the alkyl group permits growth of the algae in all test cultures.
- Alkylamine ferricyanides and ferrocyanides of the invention which contain more than six carbon atoms in the alkyl group are found to be elfective in controlling algae.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50418165A | 1965-10-23 | 1965-10-23 | |
| US510700A US3291684A (en) | 1965-10-23 | 1965-11-30 | Control of bacteria and fungi with amine cyanoferrates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3429907A true US3429907A (en) | 1969-02-25 |
Family
ID=27054752
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US504181A Expired - Lifetime US3429907A (en) | 1965-10-23 | 1965-10-23 | Amine cyanoferrates and methods for preparing same |
| US510700A Expired - Lifetime US3291684A (en) | 1965-10-23 | 1965-11-30 | Control of bacteria and fungi with amine cyanoferrates |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US510700A Expired - Lifetime US3291684A (en) | 1965-10-23 | 1965-11-30 | Control of bacteria and fungi with amine cyanoferrates |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US3429907A (enrdf_load_stackoverflow) |
| BE (1) | BE688678A (enrdf_load_stackoverflow) |
| CH (1) | CH479630A (enrdf_load_stackoverflow) |
| DE (1) | DE1543322A1 (enrdf_load_stackoverflow) |
| ES (1) | ES332591A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1116898A (enrdf_load_stackoverflow) |
| NL (1) | NL6614712A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3443924A (en) * | 1965-10-23 | 1969-05-13 | American Cyanamid Co | Method for control of algae growth |
-
1965
- 1965-10-23 US US504181A patent/US3429907A/en not_active Expired - Lifetime
- 1965-11-30 US US510700A patent/US3291684A/en not_active Expired - Lifetime
-
1966
- 1966-10-03 GB GB44076/66A patent/GB1116898A/en not_active Expired
- 1966-10-19 NL NL6614712A patent/NL6614712A/xx unknown
- 1966-10-21 ES ES0332591A patent/ES332591A1/es not_active Expired
- 1966-10-21 BE BE688678D patent/BE688678A/xx unknown
- 1966-10-24 DE DE19661543322 patent/DE1543322A1/de active Pending
- 1966-10-24 CH CH1537166A patent/CH479630A/de not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| CH479630A (de) | 1969-10-15 |
| US3291684A (en) | 1966-12-13 |
| NL6614712A (enrdf_load_stackoverflow) | 1967-04-24 |
| BE688678A (enrdf_load_stackoverflow) | 1967-04-21 |
| GB1116898A (en) | 1968-06-12 |
| DE1543322A1 (de) | 1969-10-02 |
| ES332591A1 (es) | 1967-11-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4225529A (en) | Compositions containing platinum | |
| US2686798A (en) | Metal complexes of aliphatic diamines | |
| Rauf et al. | Synthesis, spectroscopic characterization, DFT optimization and biological activities of Schiff bases and their metal (II) complexes | |
| US4200583A (en) | New platinum complex | |
| CA1117543A (en) | Compositions containing platinum | |
| US4203912A (en) | Compositions containing platinum | |
| US4329299A (en) | Composition of matter containing platinum | |
| EP0046139A1 (de) | Verwendung von Triazincarbonsäuren als Korrosionsinhibitoren für wässrige Systeme | |
| EP0169645A1 (en) | Platinum co-ordination compounds | |
| CH629744A5 (de) | Verfahren zur herstellung von neuen platin(iv)-koordinationsverbindungen. | |
| EP0799229B1 (en) | Dimercapto-1,3-dithiolo-2-one or thione maleimides, compositions containing them and their use as antimicrobial and marine antifouling agents | |
| US3429907A (en) | Amine cyanoferrates and methods for preparing same | |
| US3443924A (en) | Method for control of algae growth | |
| DE1927473A1 (de) | Verfahren zur Herstellung von Phenazin-N,N-dioxiden | |
| DE69032752T2 (de) | Verfahren zur Herstellung von Metallkomplexen von Thiolactamen | |
| US3027371A (en) | Molybdenum-containing derivatives of 1-hydroxy-2-pyridinethiones and method of preparing same | |
| US3725443A (en) | Process for the production of an alkylene bis-dithiocarbamate | |
| Liu et al. | Catalyst-and solvent-free synthesis, characterization, biological activity of Schiff bases and their metal (II) complexes derived from ferrocene | |
| Chaudhary et al. | Studies on therapeutically relevant tin (II) and lead (II) complexes of Schiff base macrocyclic ligands containing thiosemicarbazone moiety | |
| GB2093451A (en) | Nitroimidazole derivatives | |
| Narang et al. | Synthesis, Characterization, IR Spectra and Other Studies of Some Mercury (II) Chloride, Nitrate and Thiocyanate Complexes of Organic Acid Hydrazides and Hydrazones | |
| EP0018100B1 (en) | Substituted aromatic biologically active compound, a process for its preparation and its use as biocide | |
| Foye et al. | Copper complexes of aromatic dithiocarbamates and their antifungal activity | |
| Gaur et al. | Synthesis and biological properties of organotin and organosilicon derivatives using microwave irradiations | |
| Mamba | Synthesis, characterization and applications of dithiocarbamate transition metal complexes |